Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct decreasing order of the indicated C - O bond lengths in the following molecules: (I) (II) (III)
Options
- A(I) > (II) > (III)
- B(III) > (I) > (II)
- C(II) > (III) > (I)
- D(I) > (III) > (II)
Correct answer
C. (II) > (III) > (I)
Step-by-step solution
The bond lengths depend on the bond order and the hybridization of the carbon atom involved: 1. In molecule (I) (acetone), the indicated bond is a pure C=O double bond. Double bonds are the shortest among the three. 2. In molecule (II) (dimethyl ether), the indicated bond is a pure C-O single bond between an sp^3 hybridized carbon and oxygen. Single bonds are the longest. 3. In molecule (III) (anisole), the indicated bond is between the sp^2 hybridized carbon of the benzene ring and the oxygen atom. The lone pair o